HRP20040979A2 - Lansoprazole polymorphs and processes for preparation thereof - Google Patents
Lansoprazole polymorphs and processes for preparation thereofInfo
- Publication number
- HRP20040979A2 HRP20040979A2 HR20040979A HRP20040979A HRP20040979A2 HR P20040979 A2 HRP20040979 A2 HR P20040979A2 HR 20040979 A HR20040979 A HR 20040979A HR P20040979 A HRP20040979 A HR P20040979A HR P20040979 A2 HRP20040979 A2 HR P20040979A2
- Authority
- HR
- Croatia
- Prior art keywords
- lansoprazole
- crystalline solid
- solid form
- crystalline
- carried out
- Prior art date
Links
- 229960003174 lansoprazole Drugs 0.000 title claims description 250
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 title claims description 250
- 238000000034 method Methods 0.000 title claims description 72
- 238000002360 preparation method Methods 0.000 title claims description 43
- 230000008569 process Effects 0.000 title claims description 17
- 239000007787 solid Substances 0.000 claims description 83
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 43
- 239000002904 solvent Substances 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 238000002955 isolation Methods 0.000 claims description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- 238000001035 drying Methods 0.000 claims description 21
- 238000001157 Fourier transform infrared spectrum Methods 0.000 claims description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 17
- 238000010521 absorption reaction Methods 0.000 claims description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
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- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 229960005019 pantoprazole Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000000612 proton pump inhibitor Substances 0.000 description 1
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 1
- 229960004157 rabeprazole Drugs 0.000 description 1
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 1
- 235000005493 rutin Nutrition 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229940057977 zinc stearate Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36782002P | 2002-03-27 | 2002-03-27 | |
| PCT/US2003/009261 WO2003082857A2 (en) | 2002-03-27 | 2003-03-27 | Lansoprazole polymorphs and processes for preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20040979A2 true HRP20040979A2 (en) | 2005-06-30 |
Family
ID=28675405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20040979A HRP20040979A2 (en) | 2002-03-27 | 2004-10-18 | Lansoprazole polymorphs and processes for preparation thereof |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20040010151A1 (is) |
| EP (1) | EP1476442A2 (is) |
| JP (1) | JP2005533755A (is) |
| KR (1) | KR20040093187A (is) |
| CN (1) | CN1681802A (is) |
| AU (1) | AU2003224779A1 (is) |
| CA (1) | CA2480352A1 (is) |
| HR (1) | HRP20040979A2 (is) |
| IL (1) | IL164153A0 (is) |
| IS (1) | IS7467A (is) |
| MX (1) | MXPA04009384A (is) |
| NO (1) | NO20044606L (is) |
| PL (1) | PL373539A1 (is) |
| WO (1) | WO2003082857A2 (is) |
| ZA (1) | ZA200407799B (is) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6489346B1 (en) * | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| US6699885B2 (en) * | 1996-01-04 | 2004-03-02 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and methods of using same |
| US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
| US6645988B2 (en) * | 1996-01-04 | 2003-11-11 | Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| US8697094B2 (en) | 2002-10-16 | 2014-04-15 | Takeda Pharmaceutical Company Limited | Stable solid preparations |
| JP5173191B2 (ja) | 2004-09-13 | 2013-03-27 | 武田薬品工業株式会社 | 酸化化合物の製造方法及び製造装置 |
| EP1681056A1 (en) * | 2005-01-14 | 2006-07-19 | Krka Tovarna Zdravil, D.D., Novo Mesto | Process for preparing lansoprazole |
| KR100758600B1 (ko) * | 2006-01-05 | 2007-09-13 | 주식회사 대웅제약 | 란소프라졸 결정형 ａ의 제조방법 |
| JP2008543953A (ja) * | 2006-04-20 | 2008-12-04 | テバ ファーマシューティカル インダストリーズ リミティド | エスゾピクロン結晶形態ａ、実質的に純粋なエスゾピクロン及び光学的に豊富なエスゾピクロンを調製するための方法 |
| EP2089379A4 (en) * | 2006-12-07 | 2010-04-21 | Hetero Drugs Ltd | NEW CRYSTALLINE SHAPE OF LANSOPRAZOLE |
| RU2466129C2 (ru) | 2006-12-29 | 2012-11-10 | Ил Янг Фармасьютикал Компани, Лтд. | Твердые формы рацемического илапразола |
| IT1391758B1 (it) * | 2008-11-11 | 2012-01-27 | Dipharma Francis Srl | Procedimento per la preparazione di dexlansoprazolo amorfo |
| IT1392813B1 (it) | 2009-02-06 | 2012-03-23 | Dipharma Francis Srl | Forme cristalline di dexlansoprazolo |
| KR20100101405A (ko) * | 2009-03-09 | 2010-09-17 | 한미홀딩스 주식회사 | 비결정형의 (+)-란소프라졸 제조방법 및 이에 사용되는 (+)-란소프라졸 알코올레이트 |
| WO2011004387A2 (en) * | 2009-06-18 | 2011-01-13 | Matrix Laboratories Ltd | Process for the preparation of dexlansoprazole polymorphic forms |
| CN102108076B (zh) * | 2009-12-23 | 2014-07-23 | 江苏豪森医药集团有限公司 | 制备无定形右兰索拉唑的方法 |
| US8853411B2 (en) | 2010-03-31 | 2014-10-07 | Ranbaxy Laboratories Limited | Process for the preparation of dexlansoprazole |
| EP2663306A4 (en) * | 2011-01-12 | 2014-01-01 | Hetero Research Foundation | POLYMORPHS OF DEXLANSOPRAZOLE SALTS |
| MX2021001169A (es) | 2013-11-15 | 2023-02-10 | Akebia Therapeutics Inc | Formas sólidas de ácido {[5-(3-clorofenil)-3-hidroxipiridin-2-carb onil]amino}acético, composiciones, y usos de las mismas. |
| CN103664889B (zh) * | 2013-12-19 | 2014-11-19 | 悦康药业集团有限公司 | 一种兰索拉唑化合物 |
| CN104844576B (zh) * | 2015-04-28 | 2017-03-08 | 山东罗欣药业集团股份有限公司 | 一种兰索拉唑或右旋兰索拉唑晶型化合物及其制备方法 |
| CN104829594A (zh) * | 2015-05-15 | 2015-08-12 | 苗怡文 | 一种治疗胃溃疡的药物兰索拉唑化合物 |
| CN104958276A (zh) * | 2015-07-30 | 2015-10-07 | 青岛蓝盛洋医药生物科技有限责任公司 | 一种治疗胃溃疡的药物兰索拉唑组合物胶囊 |
| CN104997738A (zh) * | 2015-08-10 | 2015-10-28 | 青岛蓝盛洋医药生物科技有限责任公司 | 一种治疗胃病的药物兰索拉唑组合物干混悬剂 |
| CN107011328B (zh) * | 2017-05-05 | 2019-10-15 | 广州大光制药有限公司 | 一种兰索拉唑化合物的晶型及其结晶制备方法 |
| CN108794450B (zh) * | 2018-07-24 | 2022-08-19 | 浙江恒康药业股份有限公司 | 制备无定型右旋兰索拉唑的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK171989B1 (da) * | 1987-08-04 | 1997-09-08 | Takeda Chemical Industries Ltd | Fremgangsmåde til fremstilling af 2-(2-pyridylmethylsulfinyl)-benzimidazoler |
| TW385306B (en) * | 1996-11-14 | 2000-03-21 | Takeda Chemical Industries Ltd | Method for producing crystals of benzimidazole derivatives |
| TWI289557B (en) * | 1999-06-17 | 2007-11-11 | Takeda Chemical Industries Ltd | A crystal of a hydrate of (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole |
| PL333847A1 (en) * | 1999-06-18 | 2001-01-02 | Inst Farmaceutyczny | Crystalline forms of lansoprozole and method of obtaining lansoprazole in pharmacologically advanthageous crystalline form |
| WO2001002389A1 (fr) * | 1999-06-30 | 2001-01-11 | Takeda Chemical Industries, Ltd. | Cristaux de composes benzimidazole |
| KR100887912B1 (ko) * | 2000-12-01 | 2009-03-12 | 다케다 야쿠힌 고교 가부시키가이샤 | (ｒ)- 또는 (ｓ)-란소프라졸의 결정화 방법 |
| WO2002062786A1 (en) * | 2001-02-02 | 2002-08-15 | Teva Pharmaceutical Industries Ltd. | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1h-benzimidazoles |
-
2003
- 2003-03-27 KR KR10-2004-7015088A patent/KR20040093187A/ko not_active Application Discontinuation
- 2003-03-27 CA CA002480352A patent/CA2480352A1/en not_active Abandoned
- 2003-03-27 IL IL16415303A patent/IL164153A0/xx unknown
- 2003-03-27 JP JP2003580323A patent/JP2005533755A/ja active Pending
- 2003-03-27 CN CNA038120372A patent/CN1681802A/zh active Pending
- 2003-03-27 MX MXPA04009384A patent/MXPA04009384A/es not_active Application Discontinuation
- 2003-03-27 WO PCT/US2003/009261 patent/WO2003082857A2/en active Application Filing
- 2003-03-27 EP EP03721469A patent/EP1476442A2/en not_active Withdrawn
- 2003-03-27 AU AU2003224779A patent/AU2003224779A1/en not_active Abandoned
- 2003-03-27 PL PL03373539A patent/PL373539A1/xx not_active Application Discontinuation
- 2003-03-27 US US10/401,057 patent/US20040010151A1/en not_active Abandoned
-
2004
- 2004-09-23 IS IS7467A patent/IS7467A/is unknown
- 2004-09-28 ZA ZA200407799A patent/ZA200407799B/en unknown
- 2004-10-18 HR HR20040979A patent/HRP20040979A2/hr not_active Application Discontinuation
- 2004-10-26 NO NO20044606A patent/NO20044606L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20040093187A (ko) | 2004-11-04 |
| US20040010151A1 (en) | 2004-01-15 |
| NO20044606L (no) | 2004-10-26 |
| WO2003082857A2 (en) | 2003-10-09 |
| WO2003082857A3 (en) | 2003-12-18 |
| IS7467A (is) | 2004-09-23 |
| IL164153A0 (en) | 2005-12-18 |
| CN1681802A (zh) | 2005-10-12 |
| ZA200407799B (en) | 2006-07-26 |
| MXPA04009384A (es) | 2005-01-25 |
| PL373539A1 (en) | 2005-09-05 |
| EP1476442A2 (en) | 2004-11-17 |
| CA2480352A1 (en) | 2003-10-09 |
| JP2005533755A (ja) | 2005-11-10 |
| AU2003224779A1 (en) | 2003-10-13 |
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